Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C21H27N7O |
| Molecular Weight | 393.4854 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CCC(CC1)NC2=NC(NC3=CC=C(C=C3)N4CCOCC4)=NC5=C2N=CN5
InChI
InChIKey=ZFLJHSQHILSNCM-UHFFFAOYSA-N
InChI=1S/C21H27N7O/c1-2-4-15(5-3-1)24-20-18-19(23-14-22-18)26-21(27-20)25-16-6-8-17(9-7-16)28-10-12-29-13-11-28/h6-9,14-15H,1-5,10-13H2,(H3,22,23,24,25,26,27)
| Molecular Formula | C21H27N7O |
| Molecular Weight | 393.4854 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18483302
https://www.ncbi.nlm.nih.gov/pubmed/22477067
Curator's Comment: Description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/18483302
https://www.ncbi.nlm.nih.gov/pubmed/22477067
First synthesized in 2004 by the group of Peter G. Schultz, reversine is a 2,6- diamino substituted purine showing a potent inhibition on Aurora B, a protein kinase overexpressed in a variety of solid tumors. Due to its relevance in the cell cycle regulation, Aurora B represents a good target for anti-cancer drug development, so that reversine can be used as a promising lead compound for new potential antitumor agents. Reversine is a potent human A3 adenosine receptor antagonist with Ki of 0.66 μM, and a pan-aurora A/B/C kinase inhibitor with IC50 of 12 nM/13 nM/20 nM, respectively. Reversine also inhibits Mps1. Reversine is effective in inhibiting the growth of thyroid cancer cells by cell cycle arrest or apoptosis, especially with the more aggressive ATC and PDTC. Apoptosis was induced by the mitochondria-independent pathway. Reversine is being under investigation in clinical therapeutics.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL256 |
0.66 µM [Ki] | ||
Target ID: CHEMBL4722 |
12.0 nM [IC50] | ||
Target ID: CHEMBL2185 |
13.0 nM [IC50] | ||
Target ID: CHEMBL3935 |
20.0 nM [IC50] | ||
Target ID: CHEMBL3983 |
6.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Dedifferentiation? What's next? | 2004 Apr |
|
| Stem cells from differentiated cells. | 2004 Apr |
|
| Unraveling the molecular basis for regenerative cellular plasticity. | 2004 Aug |
|
| Small molecules, big plans--can low-molecular-weight compounds control human regeneration? | 2004 Aug 6 |
|
| Dedifferentiation of lineage-committed cells by a small molecule. | 2004 Jan 21 |
|
| "Reversine" and its 2-substituted adenine derivatives as potent and selective A3 adenosine receptor antagonists. | 2005 Jul 28 |
|
| Small molecules driving myotube fission. | 2005 Oct |
|
| Reversine-treated fibroblasts acquire myogenic competence in vitro and in regenerating skeletal muscle. | 2006 Dec |
|
| The 2,6-disubstituted purine reversine induces growth arrest and polyploidy in human cancer cells. | 2007 Dec |
|
| Induction of growth arrest and polycomb gene expression by reversine allows C2C12 cells to be reprogrammed to various differentiated cell types. | 2007 Dec |
|
| Reversine inhibits spontaneous synaptic transmission in cultured rat hippocampal neurons. | 2007 Jun |
|
| Reversine stimulates adipocyte differentiation and downregulates Akt and p70(s6k) signaling pathways in 3T3-L1 cells. | 2007 Jun 29 |
|
| Detection and functional characterization of Pgp1 (ABCB1) and MRP3 (ABCC3) efflux transporters in the PLHC-1 fish hepatoma cell line. | 2007 Mar 30 |
|
| Reversine, a novel Aurora kinases inhibitor, inhibits colony formation of human acute myeloid leukemia cells. | 2008 May |
|
| The Aurora B kinase activity is required for the maintenance of the differentiated state of murine myoblasts. | 2009 Feb |
|
| Reversine increases the plasticity of lineage-committed cells toward neuroectodermal lineage. | 2009 Jan 30 |
|
| Proteomic signature of reversine-treated murine fibroblasts by 2-D difference gel electrophoresis and MS: possible associations with cell signalling networks. | 2009 Jun |
|
| Proteomic analysis of blastema formation in regenerating axolotl limbs. | 2009 Nov 30 |
|
| Tumor cell-specific bioluminescence platform to identify stroma-induced changes to anticancer drug activity. | 2010 Apr |
|
| Beneficial effects of reversine on in vitro development of miniature pig somatic cell nuclear transfer embryos. | 2010 Apr |
|
| Reversine enhances generation of progenitor-like cells by dedifferentiation of annulus fibrosus cells. | 2010 Apr |
|
| Cell reprogramming: expectations and challenges for chemistry in stem cell biology and regenerative medicine. | 2010 Aug |
|
| Dissecting the role of MPS1 in chromosome biorientation and the spindle checkpoint through the small molecule inhibitor reversine. | 2010 Jul 12 |
|
| Ontology-based meta-analysis of global collections of high-throughput public data. | 2010 Sep 29 |
Patents
Sample Use Guides
Mice: mice were orally fed with reversine 0.1 mg/kg or reversine 1.0 mg/kg
Route of Administration:
Oral
In SW579 cells, G2/M phase arrest was found in
low-dosage treatment (1 uM) with reversine. The levels of apoptosis
(both early and late apoptosis) in ARO, WRO and SW579 cells
with reversine (10 uM) treatment were SW579 > ARO>
WRO, and were SW579 0 ARO>WRO with 1 or 5 uM
reversine treatment.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:02:34 GMT 2025
by
admin
on
Mon Mar 31 19:02:34 GMT 2025
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| Record UNII |
Z499CLJ023
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| Record Status |
Validated (UNII)
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| Record Version |
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REVERSINE
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TARGET -> INHIBITOR |
ANTAGONIST
IC50
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
